


Mistakes Sometimes Lead to Good Things

by NerdySamSays



Category: Supernatural
Genre: Alternate Universe - College/University, Christmas, Drunken Confessions, First Kiss, I have no idea, M/M, Mention of Cat, Underwear
Language: English
Status: Completed
Published: 2020-12-04
Updated: 2020-12-04
Packaged: 2021-03-10 01:47:53
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,918
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27876333
Author URL: https://archiveofourown.org/users/NerdySamSays/pseuds/NerdySamSays
Summary: A very drunk Dean decides to break into his friend's house to steal his underwear to take home for the Christmas Holidays...
Relationships: Castiel/Dean Winchester
Comments: 5
Kudos: 52





	Mistakes Sometimes Lead to Good Things

**Author's Note:**

> Before you read, please note that the quality of this fic may decrease at some point. I started writing this late last year and just finished it now. It has not been Beta read because I have anxiety and therefore no friends who can beta read things. Finishing this fic was to try and help myself return to writing as I haven't been in a good place and I wanted to try and at least finish something. So please be kind in the comments but constructive criticism is greatly appreciated. And just to see if anyone is reading this, if you don't have constructive criticism, comment down below what you want for Christmas, I've asked for a copy of the book Witchmark by C.L. Polk and a puppy (I sincerely doubt I will get a puppy, but I'm trying to wear down my parents... I'm 22... I can look after a puppy). Sorry this was longer than I meant... bye.

Some decisions, by nature, are exceedingly dumb. And at the ripe old age of twenty-one, Dean Winchester had made more dumb decisions than he would care to admit, but on the 19th of December, he was about to make the dumbest decision he would ever make. Not only did it breech his friend’s privacy, but it was just an overall terrible, stupid and childish idea. On the 19th of December, five days from Christmas, he was going to steal his best friend, Castiel’s, underwear.

Yeah… that kind of bad idea.

The day after tomorrow, Dean would be flying home to Kansas for Christmas, and wouldn’t be able to see Castiel for two full weeks. And to the drunken mind of the twenty-one-year-old, this was a perfectly reasonable memento of his friend to take. Not a picture or something the other man could have willingly gave him, no, it had to be his underwear. This was for reasons still yet unknown, at least to Dean Winchester, who was heavily in denial about his crush on his best friend. Who, for the last twenty minutes, had been attempting to shimmy up the drain pipe to access Castiel’s room from the outside.

However, in case you have never been drunk before, your motor-skills are not at peak condition, no matter how much tequila you drink. Let it also be mentioned, that Dean was friends with all four tenants, the landlord and had a rather good rapport with the house cat affectionately known as Mr. Munchies, and did not need to break in to get the underwear as he was in possession of a key.

It would be nearing on twelve am when Dean would finally realise that the kitchen window was not only lower than the bedroom window, but the lock had been broken in a particularly heated nerf war. They were still finding nerf bullets around the house in some unlikely areas. It would take Dean another half hour to figure out how to get through the window without breaking anything. He would break three mugs and a plate getting in.

It should be noted, despite the late hour, Castiel Novak was in fact not asleep but in the bathroom, neck deep in a hot bath. So, when Dean made his way upstairs to find Castiel’s bedroom dark, he was sensible enough to assume Castiel was deep asleep and not turn the light on. However, this made it rather had to distinguish what was what, and he fumbled around for a few minutes in the dark before finding Castiel’s drawers. Castiel however, at the time Dean would manage to find which drawer contained his desired prize, would return to his room; with only a towel wrapped around his waist. To find a rather splotchy faced Dean stretching a pair of batman briefs and staring at them as though they were fine diamonds.

As Castiel flicked on the light, Dean flinched, hissing at the sudden brightness of the room. “Dean?” Castiel asked, not quite realising how drunk his friend who stood before him was. Dean held up his finger to his lips.  
“Shh you’ll wake Cas,” Dean slurred, however to make it easier on you, the reader, I have translated Dean’s words to the best of my abilities. As it dawned on Castiel that his friend drunk, Dean kept riffling through Castiel’s underwear drawer, looking for the perfect pair of underwear to take with him. He pulled out a pair of rather ratty boxers, the kind that you walk around holding up but never seem to throw away before throwing it behind him like a petulant child.   
“What are you looking for there, Dean?” Castiel asked, lips quirking as his drunk friend pulled out yet another pair of his underwear and stretched them slightly before returning them to the messy drawer. A drawer, I should mention, that was perfectly neat before Dean had arrived.   
“Memento,” was all Dean offered, pulling out another pair and giving them the same treatment before deciding that they were the pair he was going to take. Castiel held his hand over his mouth and stifled a giggle, Dean’s face looked so innocent.  
“Of what?”   
“Of Cas.”   
“Why do you need one?” Castiel moved towards Dean, holding the towel around his hips, ready to take the underwear off his friend and put the drunk man to bed.   
“Like him.” Dean’s simple answer stopped Castiel in his tracks, his mouth falling open ever so slightly. Breath hitching in his chest like a love stuck school girl seeing her third crush of the week push his hair back in just the right way.   
“Okay, I’m going now,” Dean made his way towards the door where Castiel stood, still in his towel. “Cas! When did you wake up?” he asked, finally realising who he had been talking to the entire time. He stared at his friend’s chest for a moment, swallowing thickly as he tried to hid the underwear behind his back.   
“What do you mean by you like me?” Castiel asked, walking towards Dean once more, standing less than a safe distance away from the drunk man, and closing the door behind him to close them into his room.   
“I…” Dean unfortunately would not be able to finish that sentence that night as he fell into Castiel, passing out from all the alcohol in his system. Castiel had been cheated out of an answer that by this point everyone should have figured out by now. Which, was that Dean Winchester, of Lawrence, Kansas, was completely, madly, head-over-heals, and every other cliché in the book, in love with Castiel. And the only two who had not figured this out, was the two, rather dense, men themselves.

The next morning, Dean would wake up in Castiel’s bed, the other man would not be there when he woke up. Dean, who had shimmied out of his clothes in a drunken state somewhere between him passing out and him waking up, immediately thought the worst. He had not had a one-night stand with the love of his life whilst completely hammered, although his very painful brain did not remember the goings on of the previous night and had jumped to this conclusion because naturally waking up naked is going to set off some alarm bells.

Rolling out of his friend’s bed he found his waist to be hurting, which spiked his fears some more, however dear reader let me remind you of his attempts to climb the drain pipe the knight before, and let me remind you that falling can in fact hurt. Getting dressed was a mission, his clothes were tangled up in the blankets, and his socks were seemingly gone for good. Just as he was about to open the door it opened up and smacked him right in the face. Karma perhaps, Dean decided as he rubbed his now sore face. “Dean, you’re up!” Castiel sounded surprised, and Dean looked at him with sheepish eyes. The other man held up a glass of water and some Panadol, and Dean, with a polite grimace, accepted it.   
“So,” Dean began after chugging the water, he elongated the o, trying to figure out where to begin in his quest for redemption, hoping to find the right words to not completely end his friendship. “What exactly… what exactly happened last night? I mean I can guess some things, my waist fucking kills and I don’t even want to begin to question where my socks are…”  
“Dean we didn’t have sex if that’s what you’re worried about,” Castiel stated simply, hiding a gummy smile by ducking his head, “you broke in whilst drunk, I slept on the couch after you passed out in here.”   
“Then why does my waist hurt?”   
“According to a very amused Gabriel you were attempting to climb the drainage pipe and kept falling, Gabriel also mentioned offering to let you in.” Dean turned beet red, a vague, blurry image of Gabriel at the kitchen window appearing in his mind.   
“And my socks?”  
“With your shoes by the door.” Dean huffed a sigh of relief and sat back on the bed, clutching his thumping head in his shaking hands.   
“Oh, thank god.” Dean flinched slightly as Castiel sighed and sat down beside Dean on the bed, the bed dipping towards the other man.   
“Seeing as you don’t seem to remember, I’m going to be direct as ask as plainly as possible,” Castiel sounded nervous, which made Dean nervous. Dean tried to wrack his memory as quickly as he could, but turning up nothing and making his brain hurt even more, “you said you like me, is-is that true?”

Dean, being a complete and utter moron, proceeded to choke on his own tongue. A feat few can truly master. After a rather severe coughing fit, Dean stared at his friend, heart hammering in time with his head, both hurting simultaneously. “I-I’m sorry, I know you’re gay, and that doesn’t mean you have to like me back, I really never intended to admit it to you honestly. People do stupid things when drunk, say stupid things. I should just go; I have to make sure I’m ready to go home tomorrow. I hope you have a lovely Christmas, and that you get exactly what you wished for. I’m going. Bye.” Before Dean could escape Castiel’s room however, Castiel caught his wrist in a gentle but firm grip, making Dean’s dumb bitch brain splutter, and his heart flutter, and his legs feel like melting butter, and all the other appropriate rhymes.   
“Dean, I like you too,” Castiel laughed, grinning harder than he ever had. And unlike in the television show, this will not end with him dying, in this house we respect our gays and would not kill them right after the confession, let alone kill them by confession because holy mother fucking god that was… eventful. “I have since the moment I met you, I mean how could I not, you’re amazing. You do stupid things sometimes, like break into my house to steal my underwear.”  
“I did what?”  
“But you’re also one of the smartest people I’ve ever met, and I get my Christmas wish coming true every second I spend with you.”  
“Very chick flick moment of you,” Dean’s voice cracked nervously, his face going bright red as Castiel stepped into his personal space, face hovering closely to Dean’s. Dean could smell chocolate and mint on Castiel’s breath, making his heart flutter. Thankfully they were both too love struck to realise how terrible Dean’s own breath smelt, both lost in each other’s eyes, hearts pounding as their fingers intertwined.   
“Shut up,” Castiel breathed, “you know you love chick flicks.” And with the last syllable their lips touched for a moment of pure bliss. Which was then ruined by Castiel finally noticing Dean’s horrendous breath. “You need a toothbrush and some coffee.” Dean laughed. Castiel stepped towards the door and leant against the doorframe with a smug grin.   
“Coffee sounds amazing.” Dean agreed, stepping through the door and blushing as their hands brushed against each other.   
“Oh, and Dean,” Castiel whispered in his ear when he got close enough, “if you’re taking a pair of my underwear, it’s only fair I get a pair of yours.” And oh boy if you thought Dean was red before that, he lit up like a Christmas tree on fire after that one, and Castiel walked away with the biggest smile on his face.

END


End file.
